The Diary of a CEODavid Gandy: Highest Paid Male Model Opens Up About Insecurities & Imposter Syndrome | E102
CHAPTERS
- 0:00 – 3:30
Opening, Setup And The Question Of ‘Why Him?’
Steven Bartlett introduces David Gandy, emphasizing the gap between public perception of a ‘perfect’ male model and the reality of his insecurities, imposter syndrome, and new entrepreneurial chapter. He frames the conversation around what has really driven Gandy’s success across modeling and business and why his story is unexpectedly relatable.
- •Tour plug and show intro for The Diary Of A CEO Live.
- •Steven positions David Gandy as one of the highest-paid male models and now an entrepreneur.
- •Sets up the central tension: how someone so conventionally attractive can struggle with low confidence and imposter syndrome.
- •Introduces Gandy’s new brand, David Gandy Wellwear, and hints at a vulnerable, surprising conversation.
- 3:30 – 11:30
Building A Male ‘Supermodel’ Career By Design
Gandy explains how he questioned why men didn’t occupy the same supermodel pedestal as women and identified a market gap. He recounts sacrificing lucrative catalogue work to reposition himself as a high-fashion editorial model and strategically approaching Dolce & Gabbana to create a new archetype of male modeling.
- •He wondered why male models didn’t reach the fame and financial levels of female supermodels.
- •First 5–6 years of his career were mostly catalogue/commercial work that didn’t satisfy him.
- •He observed Chrissy Teigen, Naomi Campbell and others and realized they ran their careers as businesses with teams.
- •Asked his agency head Tandy Anderson to stop all commercial work so he could aim to be “the best” in fashion.
- •Accepted a major financial hit to change how the industry perceived him.
- •Strategically rebuilt his image as editorial/fashion, leading to a meeting and campaign with Dolce & Gabbana.
- 11:30 – 22:30
Strategy vs. Luck And The Breakthrough With Light Blue
The discussion digs into how much of Gandy’s success was luck versus strategy. He details why Light Blue was career-defining and how his refusal to conform to the skinny, androgynous trend eventually became a strategic advantage when the market cycled back to his more muscular, classic look.
- •He dislikes being told he was ‘lucky’ and insists most inflection points were planned.
- •Acknowledges genetic fortune (height, looks) but notes there are many better-looking and better models on the agency board.
- •Describes Tandy Anderson’s conviction that he was “Dolce & Gabbana,” not Armani or Ralph Lauren, and how she pushed that strategy.
- •Many collaborations (e.g., with M&S) were initiated by him, not the brands.
- •For M&S, he modeled for two years to prove sales before securing a collaboration.
- •Industry trend at his entry favored small, androgynous men; he chose to stay bigger and athletic for his own wellbeing.
- •When Light Blue’s creative called for that physique, there were few contenders because most had conformed.
- •The day Light Blue launched, his phone exploded with media requests, radically accelerating his career.
- 22:30 – 31:40
Fame, Friends, Humility And Imposter Syndrome
Despite global fame, Gandy insists his friends still roast him, which keeps him grounded. He articulates his experience of imposter syndrome—constantly waiting to be ‘found out’—and why he intentionally takes on risky projects to grow, while remaining his own harshest critic.
- •His old friends treat him the same as always, teasing him using his publicly available images.
- •He sees not taking himself too seriously as protective against ego inflation.
- •Advises younger models “never believe your own hype.”
- •Openly admits to imposter syndrome: a persistent fear of being exposed as having bitten off more than he can chew.
- •He is far more critical of himself than anyone else could be, which blunts external criticism.
- •He actively chooses roles with risk—writing for Vanity Fair himself, managing collaborations, investments—to maintain integrity and growth.
- •Views failure as more educational than success.
- 31:40 – 40:40
Criticism, Trolls, Male Insecurity And Aging As A ‘Weapon’
Gandy discusses the necessity of thick skin in modeling, the depersonalized nature of castings, and how online negativity often sticks more than praise. He challenges the assumption that attractive male figures are immune to insecurity, sharing his own physical worries and noting how aging is weaponized in online culture.
- •Explains that casting rejections are usually about fit to a brief, not personal worth.
- •Has experienced demoralizing castings where bookers barely look up, but tries to overcompensate with kindness when he’s casting others.
- •Says his organic fan base is largely positive, but acknowledges how one negative comment can outweigh 100 compliments cognitively.
- •Rejects the idea that male models have no insecurities; insists everyone has them.
- •Admits to physical insecurities (nose, ears, the prospect of looking like the ‘BFG’).
- •Observes that age is increasingly used as an insult online—people comparing him unfavorably to his 20-years-younger images.
- •He’s relatively unfazed by aging, seeing it as gaining wisdom and self-acceptance.
- 40:40 – 51:40
Not Fitting In: Bullying, Individualism And Rethinking Confidence
Gandy reflects on hating parts of school, being bullied, and never feeling like he fit neatly into groups. He links that stubborn individualism—refusing to join packs or follow trends—to later advantages in his career, including creative ways he stood out at castings, while clarifying that his confidence is situational and not the extroversion people assume.
- •School triggered anxiety associations; he still feels uneasy hearing the Antiques Roadshow music because it reminds him of unfinished homework and dread.
- •Enjoyed primary school but not much of secondary; was bullied and felt he didn’t fit in.
- •Attributes some of that to being an independent thinker who wouldn’t change himself to join groups.
- •Notes society’s tendency to pigeonhole people and treat difference as ‘strange.’
- •In New York casting trips, he deliberately avoided the ‘pack’ of models, flipping his schedule to arrive alone and fresher in bookers’ eyes.
- •Clarifies he’s not lacking confidence entirely; he knows his limits but likes to push them in some areas.
- •Contrasts public stereotypes of him—extroverted, boisterous—with his reality as a more reserved, strategic introvert.
- 51:40 – 1:02:20
Red Carpets, Social Exhaustion And The Desire To Be Behind The Camera
Despite a career built on visibility, Gandy finds red carpets and public-facing events draining and unnatural. He prefers being in character on set or working behind the camera as a creative director, describing how social situations sap his energy while solitude—long walks with dogs, travel alone—restores him.
- •He dreads red carpets even after doing them for years, describing them as an unnatural environment.
- •Feels more comfortable when he can ‘play a role’ for a brand campaign than when he appears as himself at events.
- •His partner Steph loves events, but he jokes he’ll always ‘win’ the silent treatment because he can happily go days not talking.
- •Events drain him; he often skips red carpets to head straight inside to have targeted conversations instead.
- •Loves long solitary walks and being alone; identifies as naturally a loner.
- •Enjoys working as a creative director for shoots and even turned down being in front of the camera for a RAF/Breitling film he directed.
- •Believes he wasn’t the ‘right casting’ for certain roles (e.g., Hercules-style parts, Fifty Shades of Grey) and admires actors like Jamie Dornan, accepting he couldn’t match their acting level.
- 1:02:20 – 1:10:00
Mental Health: Dark Periods, Bipolar Up Close And Men Talking
Gandy describes experiencing his own milder ‘dark periods’ and having close relationships with people later diagnosed with bipolar, which exposed him to severe mental illness firsthand. These experiences underpin his involvement with men’s mental health charities like CALM and inform his belief that men need to talk and be properly listened to.
- •He hasn’t had clinical depression at severe levels but has gone through dark phases where nothing could cheer him up and he wanted isolation.
- •These episodes seemed untriggered and would eventually lift, which he frames as a chemical shift in the brain.
- •He has dated someone with bipolar disorder and seen the extremes: e.g., spending days in a room watching the same TV series for ‘safety.’
- •He learned how hard it is to support someone when you desperately want to ‘fix’ them but can’t; professional help is essential.
- •Works with men’s mental health organisations (including CALM) and sees listening—not just talking—as the missing piece.
- •Notes that many people talk but don’t really listen to others’ mental health disclosures.
- •He also has long-term poor sleep habits, often working until 2 a.m., which intertwine with his driven work ethic.
- 1:10:00 – 1:18:20
Workaholism, Happiness And The Pandemic Slowdown
The conversation turns to Gandy’s relentless work patterns, his inability to fully switch off, and how the pandemic’s enforced pause unexpectedly made him happier. Steven challenges him on whether constant striving is stealing happiness, prompting Gandy to reflect on being ‘positive’ versus ‘happy’ and the fleeting satisfaction of achievement.
- •He has never slept well, even as a child, and now routinely works late into the night after gym and errands.
- •Points to graft—working when others are relaxing—as a key factor in his success.
- •During the pandemic, when nobody could work, he felt strangely happier and less anxious about ‘falling behind.’
- •Financially he was impacted, but previous smart investments and reserves cushioned the blow.
- •He admits he truly switches off only in the week between Christmas and New Year when the world slows collectively.
- •Steven labels his constant striving a possible ‘thief of happiness’; Gandy describes himself as more “positive” than clearly “happy.”
- •He acknowledges that the feeling of achievement—whether on a shoot like Light Blue or finishing a renovation—is intense but very short-lived, then replaced by ‘what’s next?’
- 1:18:20 – 1:30:00
Creating David Gandy Wellwear: Comfort, Confidence And Sustainability
Gandy outlines the origin and philosophy of his clothing brand, David Gandy Wellwear, which aims to combine style, comfort, and psychological wellbeing. Drawing on his M&S collaboration experience and academic studies on clothing’s impact on mood and performance, he’s building a brand that uses fabric technology and thoughtful design to elevate everyday wear while challenging fast-fashion habits.
- •He’s long wanted his own brand, beyond being a ‘brand’ himself as a model.
- •His collaboration with M&S, particularly in loungewear, showed him the potential of comfortable, well-designed basics—his range became the third biggest loungewear in the UK.
- •Felt constrained by M&S’s control (only about 60% reflected his vision), which motivated creating something fully his.
- •During lockdown, his friend Charlie T pushed him to finally build the brand; Gandy became their agency’s first client.
- •Wellwear is rooted in the idea that certain clothes make you feel positive and confident; he references studies showing students perform better in comfortable clothing.
- •Discusses oxytocin’s role: soft, comforting textures (like a favourite sweatshirt) can induce positive mood.
- •Wellwear includes features like aloe vera-infused, anti-inflammatory, antibacterial fabrics (e.g., moisturizing pyjamas), and aims to combat fast-fashion’s environmental and psychological downsides by making durable, emotionally resonant pieces.
- •He is deliberately vague about the long-term vision but clearly sees Wellwear as a multi-year, evolving wellbeing brand.
- 1:30:00
Legacy, Promises And The Importance Of Men Talking
In a closing segment, Steven asks Gandy a question left by a previous guest about making the world better. Gandy responds by focusing on Wellwear’s mission to make people smile and bring positivity in a polarized world, and both men affirm the therapeutic value of honest conversation—particularly for men, who often don’t talk or truly listen.
- •Prompted by the previous guest’s question, Gandy says his promise is to use Wellwear to make people smile and inject positivity, which he sees as priceless.
- •He briefly acknowledges his charity work but doesn’t centre it as a ‘promise.’
- •Steven praises Gandy’s self-awareness and openness; Gandy notes that talking itself feels therapeutic.
- •They both highlight that men are often poor at opening up, and when people do talk, others frequently fail to truly listen.
- •Gandy suggests he might need to explore therapy to understand some of his deeper patterns (e.g., red carpet anxiety, happiness/positivity distinction).
- •They end on a note that conversations like this can be both personally healing and publicly useful.
